


Drowley Compilation

by songofhell



Category: Supernatural
Genre: M/M
Language: English
Status: In-Progress
Published: 2017-06-12
Updated: 2018-09-12
Packaged: 2018-11-13 02:10:00
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 34
Words: 12,492
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11174817
Author URL: https://archiveofourown.org/users/songofhell/pseuds/songofhell
Summary: A compilation of my drabbles and headcanons from my tumblr.





	1. Drunk

**Summary for the Chapter:**

> Prompt: Dean being a really affectionate drunk and not in the sexy way, but in the "cuddle with me right now" and "I'm going to shower you in compliments" way.

Dean getting drunk and texting Crowley, ‘You need to come over RIGHT NOW!’ And Crowley would be all worried and would teleport to Dean immediately, but Dean would just pull him into bed and snuggle up to him.

“Really, squirrel?” Crowley tried to sound exasperated, but his smile betrayed him as he wrapped his arm around Dean. “I had been in the middle of something.”

“Well, you needed to be here.” He kissed Crowley’s neck before resting his head on his shoulder.

“Oh? And why’s that?”

“Because things are better with you here. You just… you make me happy. Even when you’re being irritating, I’m glad you’re around.”

Crowley chuckled. “I’ll remember that the next time you yell at me to get out.”

“You should.” Dean looked up at him with wide, serious eyes. “I love you. I always want you around.”

He smiled softly and planted a brief kiss to his lips. “I love you, too. Now, you should get some sleep.”

“Okay,” Dean sighed and snuggled up to him again. “You know you’re the best, right?” he muttered after a minute.

“Sleep,” Crowley said sternly.

The pattern continued for a few more minutes - Dean giving Crowley a compliment, and Crowley reminding him that he was supposed to be sleeping - before Dean finally drifted off. Truth be told, Crowley enjoyed this, enjoyed seeing all the layers removed that Dean put up to hide his soft side. Sober Dean never wanted to admit just how much Crowley meant to him, so it was always good to hear.


	2. Come on Me

**Summary for the Chapter:**

> Prompt: I don't know if you've seen this post around tumblr but "I wanted a response and my mind gave me 'come at me' and 'come on' so I yelled COME ON ME" Dean saying that and then he blushes and rubs his face in his hands and Crowley just going "If you insist."

Dean’s relationship with the King of Hell had changed a lot over the years. There were times anymore when they were almost getting along. This was not one of those times.

Dean was pissed at him, something that still happened quite often, and the argument had been building for some time now.

“Do you really want to turn this into a fight, squirrel?” Crowley challenged.

Two possible responses instantly popped into Dean’s mind, combining as they came out of his mouth, so that instead of saying ‘Come at me!’ or ‘Come on!’, he yelled, “Come on me!”

It took him approximately one second to realize what he had just said, and instantly all fight left him as he turned bright red and drug his hands over his face. He took a deep breath and willed himself to peek up at Crowley.

The demon’s eyebrows were raised, an amused smile twisting his lips, telling Dean that he knew exactly what had happened. “If you insist,” he said smoothly.

“I didn’t… I meant-” Dean tried halfheartedly, but Crowley interrupted him.

“Oh, I know what you meant, but I much prefer what you said.” He strode forward, his steps confident and purposeful, coming to a stop just a short distance in front of Dean. “What do you say we forget our little disagreement and relocate this to a more suitable venue - such as, my bedroom?”

Dean’s blush deepened. “Shut up,” he muttered, not quite looking at him.

“You sure you want me to? Because _I_ think that there was some subconscious desire that drove you to say that. Care to put my theory to the test?”

He didn’t want to entertain the thought, to even consider for a second that Crowley might be right. But there must have been someone on his face, some small flicker of emotion that betrayed him. Because suddenly Crowley was kissing him, and for whatever reason, he wasn’t pulling away. Even worse, he was kissing back.

After several seconds, Crowley pulled away, smirking victoriously, and Dean said the one thing he could think to say, this time managing to get it right, although it now meant essentially the same thing as what he had previously said instead of it. “Come at me.”


	3. Team Free Will

**Summary for the Chapter:**

> Prompt: Dean considering Crowley part of Team Free Will because he fought Satan for them.

“Look at you three, all geared up and ready to go. Team Free Will, right?”

Sam, Dean, and Castiel turned as Crowley appeared behind them, his usual smug expression in place. Sam rolled his eyes as he closed the trunk of the Impala, but Dean frowned at the demon. “But that’s you, too.”

Crowley’s expression slipped, his eyebrows drawing together. “What?”

“You went toe-to-toe with Satan, I think you can be considered a part of Team Free Will.”

The shock of the words caused Crowley to rock back on his heels slightly. His eyes flickered to Sam, who was eyeing his brother with a resigned expression, and then to Castiel, who appraised him for a moment, shrugged, then moved to get into the backseat of the car.

“Well. I’m touched.” He tried to regain his usual haughtiness, but there was still a touch of surprise on his features and an undercurrent of emotion in his voice that he hated.

Dean smiled as he stepped up to clap him on the shoulder. “Welcome to the team. Now, we’ve got work to do.”


	4. Body Heat

**Summary for the Chapter:**

> Prompt: It's freezing out and Dean and Crowley have to cuddle for warmth, and Dean is embarrassed as fuck about it.

“You know, sharing body heat is more effective without clothing.”

Crowley waited for Dean’s snappy ‘Shut up,’ but it never came. When he looked at the hunter comfortably situated in his arms, his eyes were locked on the ground, his jaw set, and a mildly adorable blush was forming on his cheeks. Considering that Dean couldn’t kill him right now, unless he wanted to freeze to death, Crowley was feeling quite daring and opted to slip his hand beneath the hem of Dean’s shirt, splaying his hand over the skin of his back. Dean’s blush deepened, but he was still as resolutely silent as he had been since he had resigned himself to the fact that he had to cuddle with the King of Hell.

Crowley smirked as he leaned in the small distance necessary to bring his lips to Dean’s ear. “And then, who knows?” he breathed. “That could lead to an even more enjoyable way to stay warm.”


	5. Accent

**Summary for the Chapter:**

> Prompt: dean scoffing at crowley when they first meet and as soon as crowley opens his mouth dean thinks "shit he has a hot accent"

Dean definitely has a thing for accents, and it doesn’t take Crowley long to catch on. He sees the faintest shiver that runs down Dean’s spine whenever he speaks, or the way the hunter’s anger will fade just slightly if he says something in _just_ the right way. 

So naturally, he has fun with it. He’ll pop up behind Dean and speak right into his ear. Whenever he’s around Dean, he’ll find any opportunity to say something. The Winchesters assume that he just loves to talk, but really he just loves to watch the subtle changes in Dean’s expression. One day he vows to find out how much more extreme the reaction is when he’s whispering all the things he wants to do to him.


	6. Research

**Summary for the Chapter:**

> Prompt: Dean powering down the warding so Crowley come over. I bet that's not the first time that's happened. ;D

It does make it awkward for nights when Cas stays in the bunker; he always knows when Dean and Crowley are having sex because he feels the warding power down.

Sam: You could at least help with the research.  
Dean: Hey, I researched all night last night.  
Cas: No, you didn’t. You powered down the wards; Crowley came over last night.  
Dean: He… helped with research.  
*Sam and Cas look at him exasperatedly*

itshighnoon1200 sent: "Dean: Crowley helped with the research. So much research. We researched all night long. Sam: You need to stop."

Dean: But he was a great help. Really… hard researcher.  
Sam: What will it take to get you to stop talking?  
Dean: Hey, you’re the one who said you wanted me to do more research…  
Sam: Okay, fine, you don’t have to do research!  
Dean: Fine…. I’ll just go relax in my room then.  
*five minutes later*  
Cas: He powered down the wards again.


	7. You Idiot

**Summary for the Chapter:**

> Prompt:okay but what if Dean didn't tell Crowley he was alive after the season finale because he didn't think Crowley would give a shit and he tells Crowley this and Crowley tells him "Of course I care, you idiot."  
> Post 12x07

“This is rich, coming from someone who never told me he was alive,” Crowley snapped.

Dean’s eyebrows furrowed in confusion. “What does that have to do with anything? Why would you give a shit if I’m alive or not? It’s not like you care about me,” he added a bit bitterly.

“Of course I care, you idiot!” Crowley nearly shouted in his frustration.

Dean regarded him carefully, as though trying to figure out what he was playing at. Hell, that was probably exactly what he was doing. “Why would you care about me?” he finally asked bluntly.

Crowley shook his head, glaring at the wall on the other side of the room. “If you haven’t gotten it by now, you aren’t going to.”

“Well, maybe if you _told_ me…”

He turned his glare on the hunter. “Why bother? You’d probably just accuse me of trying to manipulate you. And it’s not like you return my feelings.”

Dean blinked in surprise. “Feelings?”

Crowley rolled his eyes. He might as well say it; he doubted very much that Dean would believe him, anyway. “I love you. Not like you care.”

Dean just stared at him in shock for a minute before he smiled wryly and took a step forward, reaching up his hand to caress Crowley’s cheek. “Of course I care, you idiot.”


	8. Pictures

**Summary for the Chapter:**

> Prompt: Dean having like 100 pictures of Crowley in his phone and Dean being really embarrassed about it when Crowley finds out.

Dean should have known better than to leave his cell phone on the bar when he went to the bathroom. But it wasn’t like he’d done it intentionally - he’d just honestly forgotten that he hadn’t put it back in his pocket after getting off the phone with Sam. It wasn’t until he was walking back out to his seat and he saw Crowley scrolling through his phone that he realized his mistake.

“Hey,” he barked. “Do you mind?”

The smirk on Crowley’s face when he looked up at him was unsettling. “Oh, not at all. On the contrary, I’m flattered.”

Dean frowned as he tried to make sense of Crowley’s words, until he realized what the demon must be looking at. “Give it back,” he snapped, already feeling his cheeks heating up.

“But I’m only halfway through,” he protested, waving the phone his his face so that he caught sight of the picture of Crowley sipping on his usual fruity drink.

Dean’s hand shot out and snatched the phone back from Crowley’s grasp. “I just... haven’t been through my phone in a while, okay?” he muttered as he exited out of his pictures and shoved the phone back in his pocket, all the while avoiding eye-contact.

“You sure about that?” Crowley pressed, his voice positively gleeful. “Sure you don’t use those pictures of me in your alone time?”

His cheeks turned even redder. _“No!”_ He shook his head, licking his lips nervously. “Look, you know we took a bunch of pictures when we were... you know. I just haven’t gotten around to deleting them.”

“Well, nor have I. I just hadn’t realized quite how many pictures you took of just me.”

Dean didn’t know what to say, so he settled on glaring at the wall.

Crowley chuckled as he rose to his feet, taking a step closer, into Dean’s personal space. “No need to be embarrassed, darling. As I said, I don’t mind.” He leaned in, his lips close to Dean’s ear. “Besides, who am I to judge? I quite enjoy my pictures of you,” he added in a low voice.

Dean swallowed thickly as he looked at him uncertainly, wondering if he meant what his words seemed to imply. But it was Crowley, of course he meant that. And Dean wasn’t sure how he felt about that. A little disturbed, yeah... but also a little aroused.

“Well, I must be off.” Crowley took a step back, drinking in the disappointment that flickered over Dean’s face. “Maybe I’ll send you some more pictures later - with less clothing, of course.” He winked before vanishing from the spot.

Dean squeezed his eyes shut, knowing full well that Crowley wasn’t going to let this go. Oh, this was not going to end well for him. But he was pretty sure that he’d enjoy the ride, at least.


	9. Say Something Romantic

**Summary for the Chapter:**

> Prompt: “Say something romantic” “I love you, you pain in the ass.”

It was their one year anniversary, and Crowley had convinced Dean to get dressed up and go out to a nice restaurant to celebrate. Unsurprisingly, Dean came in late, and if the exhaustion emanating from him was anything to go by, that day’s hunt hadn’t gone as well as he had hoped.

“Freakin’ witches,” he muttered as he sat down across from his boyfriend. “I swear, if I see one more-”

“Happy anniversary to you too, love,” Crowley interrupted pointedly.

Dean sighed, fixing him with a glare. “Really? It’s just a day, Crowley, and so far, it hasn’t been too damn happy.”

“Well, hopefully I can change that.” He was unfazed by Dean blowing off the importance of the day. He knew that if it were up to him, they wouldn’t be going out, and he also knew that the fact that he had agreed without complaint just went to show how much he loved him. “Now, say something romantic, and then you can rant away to your heart’s content.”

He rolled his eyes. “I love you, you pain in the ass.”

Crowley beamed. “I love you too, darling. Now, tell me about the witches.”


	10. Dirty Talk

**Summary for the Chapter:**

> Prompt: Crowley distracting Dean all the time by whispering dirty shit to him

Crowley had always found joy in making vulgar comments, Dean had learned that some time ago. And maybe some part of him had wondered if he was like this with everyone, or if he got the brunt of it, but for the most part, he had tried not to think about it, tried not to read too much into it. 

He should have known that things would only get worse after they started... whatever it was they were doing. It was more than just sex, Dean could definitely tell that much, but it wasn’t like they were in a relationship, either. They kept whatever it was that they were behind closed doors - or Dean tried to, at least; which proved difficult with all the comments that Crowley had taken to whispering to Dean, regardless of who was around.

For the most part, Dean loved Crowley talking dirty. His words combined with his voice was enough to make Dean come undone. There was a time and a place, though; and that time and place was not in the middle of the library while doing research with Sam!

Sam’s was focused on the book in front of him, so he didn’t notice the way Crowley’s lips had paused next to Dean’s ear as he had reached across him for a book. He did, however, hear the sharp intake of breath from his brother and when he looked up, he noticed the pink in his cheeks and the way he was biting his lip.

“Everything okay?” he asked.

“Mmhm,” Dean hummed, somehow managing to sound breathless.

Sam frowned, his gaze flickering to Crowley, who looked too innocent to not draw suspicion to himself. He sighed. It wasn’t the first time something like this had happened, and it was getting progressively harder to convince himself that nothing was going on. “Is there something you two want to tell me?” he demanded.

Crowley arched an eyebrow at Dean, while the latter shook his head. “Nope,” Dean said quickly. “Nothing to tell.”

Sam glared at him. “Dean, I’ve walked in on you watching porn, so unfortunately, I know what you look like when you’re aroused. And I highly doubt that’s from that book. Crowley, I’m going to regret asking this, but what the hell did you do?”

“Nothing,” Crowley said innocently. “I merely told him that it’s difficult to concentrate when all I can thing of is how amazing his lips look wrapped around my cock.”

Dean turned bright red as his gaze snapped to Crowley in disbelief. “Crowley!” he gasped.

Sam sprang up from the table, his book in his hand. “I’m just going to... finish this in my room.” He shook his head as he hurried from the room.

“Well, at least that’s all out in the open now,” Crowley sighed contentedly once he and Dean were alone.

Dean’s eyes grew wide. “You - are you... are you telling me, you _wanted_ him to find out?” he spluttered.

“Of course,” he shrugged. “Don’t get me wrong, darling, sneaking around is fun and all, but if this was ever going to be anything serious, your brother had to know about us.”

Dean was torn between being furious at what Crowley had done and being glad that Crowley really did want this to be something serious. “So, all along, this was your goal?”

“Yep. Took him long enough to catch on.”

He sighed, rolling his eyes. “Well, at least that means you’re done now.”

Crowley raised his eyebrows. “Oh, not at all. I no longer have to pretend to be sneaky about it.” He leaned in, brushing his lips against Dean’s ear. “You haven’t seen anything yet.”


	11. Something More - Sequel to Dirty Talk

**Summary for the Chapter:**

> Prompt: sequel to my last prompt Dean be kinda pissed that they didn't talk about Crowley's plan to just drop that fact they're banging to Sam

Dean felt he had every right to be pissed. He had been fully aware when falling into bed with Crowley that the demon was sure to press his buttons fairly often, but _this?_ He didn’t have the right to just declare to Sam that the two of them were sleeping together. It should be Dean’s choice when they broke the news to his brother.

Of course, Crowley felt that his reasoning made up for his stunt. And sure, Dean was happy that he wanted their relationship to be more serious, but he would be a lot freakin’ happier if Crowley had just _talked_ to him about it. If he’d just told him that he wanted to be more open about their relationship, Dean would have obliged. But no, he had gone and taken the matter into his own hands, and in the worst possible way, of course!

After Dean had gotten mad and stormed off, Crowley had taken to following him around, trying to get him to talk. He hadn’t even noticed when Dean had strolled right over a devil’s trap in his desire to get some space. He ignored Crowley’s shouts as walked away and shut himself in his room to think.

About an hour had passed when there was a knock at his door, and then Sam stepped inside. “Um, are you aware that your boyfriend is stuck in a devil’s trap?”

Dean groaned as he ran his hands over his face. “He’s not my boyfriend,” he muttered. Or maybe he was. He honestly wasn’t sure; he just knew that ‘boyfriend’ seemed like a weird title to attribute to Crowley.

“Could’ve fooled me.”

He looked up at his brother with tired eyes. “Just say it,” he sighed.

Sam frowned. “Say what?”

“Whatever it is that you’ve been holding in since Crowley’s outburst.”

“What, vomit? That’s passed.” He shook his head with a wry smile. “Look, I don’t get it, but... if he makes you happy...”

“He makes me furious,” Dean growled.

Sam chuckled. “Sounds like a boyfriend to me. Though, you might want to try actually talking out your problems instead of just sticking him in devil’s trap.”

“Yeah, but this is easier.” He shrugged, then paused, the corner of his lips tugging up slightly. “Was he pouting?”

“Yeah,” he muttered with a roll of his eyes. “Just go work things out, would you?”

“Fine,” he sighed, but he was smiling as he walked past Sam and made his way to where he had left Crowley. He was indeed pouting, and the sight was oddly adorable.

He quickly schooled his features into a more stern expression as he walked into the room. “Don’t ever pull something like that again.”

Crowley looked up at him hopefully. “Fine. I’m sorry. I just thought it would be funny.”

“Well, it wasn’t.” He came to a halt in front of the devil’s trap, crossing his arms over his chest. “If you want to be something more, you talk to me about it. You don’t out us to my brother.”

“Okay. I want to be something more.”

Dean pursed his lips thoughtfully and nodded. “Alright.” He pulled a knife out of his pocked and leaned down to scrape some of the paint off the floor.

“Alright?” Crowley questioned as he stepped out of the trap.

“Alright,” he repeated. He reached out and grabbed hold of his tie, pulling him in for a kiss.


	12. Emotions

**Summary for the Chapter:**

> Prompt: crowley realizing his was in love with dean some time around the mark of cain thing and going "fuck"

The plan may not have been simple, but it was doable: Convince Dean to work with him, let him do all the dirty work in tracking down Cain, show off the infamous hunter to the Father of Murder, and watch with satisfaction as Dean was given the Mark of Cain. _Technically,_ everything went according to plan. Well, everything except that last step. Dean got the Mark, all right, but it wasn’t satisfaction that Crowley felt as he watched Cain transfer it onto him.

Excitement was building in Crowley as Dean cut Cain off before he could warn him of how the Mark would change him. That was all well and good - the less Dean knew about that, the better. The two clasped each others’ forearms, and their veins glowed red as the Mark was transferred from Cain’s arm to Dean’s.

Then Dean let out a gasp of pain, clutching his arm as he doubled over slightly, and all of the joy that Crowley had been feeling left him instantaneously. Emotions that the demon wasn’t familiar with twisted in his gut as he watched the pain flash across Dean’s face. 

“Dean!” He heard a voice speak, full of concern, and he realized belatedly that it had been him.

Where was this coming from? Crowley had never felt anything but satisfaction at another person’s pain, and yet when it came to Dean... he wanted to do everything he could to take that pain away. Since when did the King of Hell have... _concern_ for a human? And not just any human, but a hunter - a Winchester?

He paid closer attention to his emotions as he watched Dean straighten up, saw the resolve harden his eyes, and he noticed something that was beneath the concern he felt - a sort of fondness. But no, that wasn’t right. It went deeper than that...

_He loved him._

Fuck. He barely stopped himself from swearing aloud as the horror of the realization washed over him. He shouldn’t come even close to loving anyone, and yet he had somehow managed to fall for the worst possible person for him to love. Not only was Dean one of the biggest threats to his kingdom, he also didn’t have much in the way of a projected life span. Oh, and he had made it perfectly clear how much he hated him, of course.

It looked like Crowley had better get used to feeling these new emotions, because he was going to be feeling a whole lot of pain in his future.


	13. Lunch Date

**Summary for the Chapter:**

> Prompt: "What should I eat for lunch." "Poison." I saw a tumblr post about that and it made me think of Drowley.

“What should I eat for lunch?” Dean asked upon hearing footsteps approaching behind him as he rummaged through the pantry.

“Poison,” a familiar voice suggested.

Dean spun around, frowning at the demon standing behind him. “What the hell are you doing here, Crowley? And that’s a little harsh, don’t you think?”

Crowley shrugged. “At the rate that you come back to life, I doubt it would do you much harm. And actually, I was hoping for a lunch date.” He offered out his hand.

Dean glanced down at the hand cautiously. “You aren’t going to try to feed me poison, are you?” he checked.

“After all the work I’ve put forth trying to keep you alive, I think that would be a bit of a waste.”

He grinned. “Then you’re payin’.” He took Crowley’s hand, and then they teleported from the bunker.


	14. Shut Up

**Summary for the Chapter:**

> Prompt: dean asking Crowley if he ever shuts up and Crowley replying with some thing about how he talks just to annoy dean (also: “I know you like the sound of my voice, squirrel.”)

Sam and Dean had had to divide forces to work a couple of different cases, so Sam and Castiel had taken one, and Dean was stuck with Crowley. Honestly, he didn’t mind working with Crowley, and it wouldn’t have been so bad, if it weren’t for the fact that the demon had insisted on riding in the Impala with him on the seven hour car ride to Springfield, Missouri, and he _wouldn’t stop talking._

An hour into the trip, Dean sighed, glaring at the red stop light in front of him. “Do you _ever_ shut up?” he demanded exasperatedly.

Crowley smirked. “Only when I’m not with you, darling.”

Dean’s eyes narrowed as he turned his glare on him. “And _what_ is that supposed to mean?”

“You’re quite adorable when you’re annoyed,” he said with a shrug. “And besides, I know you like the sound of my voice, squirrel.”

He opened his mouth then closed it again to grind his teeth together in frustration. “I don’t-”

“The light’s green,” Crowley pointed out, nodding towards the stoplight. He relaxed back in his seat as Dean accelerated. “Now, where was I?”


	15. Demon Deal

**Summary for the Chapter:**

> Prompt: dean going to the crossroads and specifically summoning crowley and when crowley asks who the deal is for dean goes "you" because that's the one thing dean wants

Crowley felt the familiar tug of a summoning and frowned. This was a _crossroads_ summoning – he shouldn’t be getting this, he was the King of Hell, it should be going to the next crossroads demon in rotation. If whoever was doing the summoning had found a way to summon him specifically, they were no run-of-the-mill desperate soul, they knew a thing or two. Intriguing.

He appeared behind the summoner, his eyebrows raising as he recognized him. “You could have called.”

Dean turned around, shifting his weight uncomfortably from one foot to the other. “Yeah, well… didn’t know if I’d be breaking some demon deal etiquette.”

“Since when do you care about breaking etiquette?” Crowley pointed out curiously.

He just shrugged, not quite looking at the demon in front of him.

“Very well,” he sighed. He didn’t know exactly why Dean would be seeking to make a demon deal, but his money was on that it had something to do with either Sam or Castiel. Dean would never be making a deal for himself, he was too selfless. “So, who is the deal for this time?”

Dean licked his lips nervously as he finally met Crowley’s eyes. “You.”

Crowley blinked. “Pardon?”

He took a step closer. “I want you,” he said clearly, no hesitation in his voice.

He looked over Dean, torn between not wanting to look a gift horse in the mouth and thinking that something _had_ to be wrong. “Are you drunk?”

“Maybe,” he muttered with a slight shrug. “Doesn’t matter. I want you just as much while sober.”

Crowley allowed himself a small, hopeful smile. “I don’t think you’d sell your soul just to get me while sober, though.”

He must have known that to be true because he ignored the statement. “So, do we have a deal or not?”

He smirked. “No.” He let that hang in the air for a second, watching with delight as disappointment colored Dean’s expression. “But I’m willing to renegotiate.”

He frowned. “Renegotiate?”

“I’m not satisfied with just your soul in exchange for myself,” Crowley explained. “I want all of you.”

Dean took a moment to process that, and then a slow smile began to spread over his face. “Sounds good to me.”

“Excellent.” He grabbed hold of Dean’s shirt and tugged him in for an enthusiastic kiss.


	16. Cause it's Fun

**Summary for the Chapter:**

> Prompt: Some random demon asks Demon!Dean if he’s sleeping with Crowley to climb the ranks of Hell and Dean replies “Nah, I sleep with him ‘cause it’s fun.”

The other demon fixed Dean with an accusatory glare. “You think sleeping with Crowley is gonna get you to climb the ranks?”

Dean’s expression was unfazed as he shrugged. “Nah, I sleep with him ‘cause it’s fun. Couldn’t care less about my rank in Hell.”

The demon blinked in surprise. “So, you admit you’re sleeping with him?”

“Well, yeah.” He smirked. “We share a hotel room, and neither of us sleep - it’s not like we’re trying to hide it.”

His eyes narrowed. “You’ve gotta be after something.”

Dean rolled his eyes. “Yeah. It’s called a good time - which Crowley never fails to provide.” He sighed as he drew out the first blade. “And this conversation is starting to bore me,” he commented nonchalantly as he ran the demon through with the blade. Crowley would no doubt throw a fit when he found out that Dean had killed another of his demons, but he knew better than anyone how to distract him. He’d get Crowley to move onto matters that Dean would much rather him focus on in no time.


	17. Jealous

**Summary for the Chapter:**

> Prompt: When Dean first seeing the picture of Bobby and Crowley making out he gets all upset and later Crowley asks me if he's jealous and Dean blushes and bristles a little and is like "NO" (He totally is jealous)

When Crowley cleared his throat and pulled out the picture of him and Bobby sealing their deal, Dean’s eyes widened in utter disbelief, his stomach tightening as he felt the urge to vomit. The image of Bobby _kissing Crowley_ was just... it was _wrong._ Bobby was like a father to him, and Crowley was... a demon.

“Why’d you have to take a picture?” Bobby sighed.

“Why’d you have to use tongue?” Crowley threw back at him with a smirk.

A wave of resentment washed over Dean as his gaze snapped back to Bobby. But no, that couldn’t be right. What reason did he have to be resentful? Disgust was probably a more accurate word. Clearly, whatever it was, though, it had shown on his face, and it hadn’t escaped Crowley’s notice.

A few hours later, when Dean and Crowley were on their way to Chicago, the demon spoke up. “Jealous?”

Dean glanced over at the passenger’s seat, his eyebrows drawn in confusion. “What would I be jealous about?”

“Oh, I just couldn’t help but notice that you seemed particularly displeased about my and Bobby’s little kiss.”

His eyebrows shot up to his hairline, even as something unpleasant churned in his stomach. “And you think I’m jealous?”

“Oh, yes.”

“Hell no!” Dean protested, shaking his head in disgust. “I couldn’t be _less_ jealous. I definitely _don’t_ want... I am _disgusted,_ that’s all it is!”

Crowley was watching him ramble with an amused smirk. “Clearly,” he murmured, obviously unconvinced.

He scoffed as he came to a stop at a stoplight. There was no way he _wanted_ to kiss Crowley. The guy was a demon - it didn’t matter how attractive he was, or that he had impressed Dean just a bit in the time they’d known each other, or that his voice was like... No, none of that made any difference. He did _not_ want to kiss him. But suddenly he was doing just that.

Crowley had taken advantage of them being stopped to pull Dean into a heated kiss, and the hunter was surprised enough that he didn’t even try to resist. On the contrary, he was kissing him back.

“There,” Crowley eventually said with satisfaction as he pulled back. “I’d hate to be the cause of any discord between you and your father-figure, so... all better?”

Dean couldn’t do anything but stare at him with wide eyes and pretend that he wasn’t finding his lips distracting. Crowley held his gaze, smirking broadly.

Finally, a car honking behind them returned his attention to the road, and he accelerated past the now green light. “We’re never speaking of this again,” he muttered.

“Fine by me,” Crowley surprisingly agreed. “Why speak when there’s so much more fun things to do?” he continued in a low voice.

Dean felt the blood rush up to his cheeks. As well as lower. Dammit. He was definitely in trouble.


	18. Wingman

**Summary for the Chapter:**

> Prompt: Dean needs a wingman and Crowley is the only one around, but when they get to the bar Crowley won't stop hitting on him.

Dean smiled at the beautiful red-head sitting next to him at the bar. “You know, your eyes are just absolutely gorgeous.”

She smiled up at him, said gorgeous eyes dancing. “Why, thank you.”

Crowley peered around from where he sat on Dean’s other side. “They’re alright,” he said with a shrug. “They’ve got nothing on yours, though.”

Dean shot the demon a glare before turning back to the woman on his right, who was looking at him with a raised eyebrow. “Sorry about him,” he sighed. “He just says whatever pops into his head.”

She opened her mouth to respond, but Crowley cut her off. “Oh no, if I did that, you’d be constantly blushing from all the things I’d be saying I want to do to you.”

Dean’s jaw dropped open slightly as he stared at him in utter disbelief - too shocked to even glare properly.

“Um... I think I’ll just leave you two alone,” the woman spoke up, getting to her feet.

“No, wait!” Dean’s gaze snapped back to her as he frantically tried to come up with a way to fix this, but she was already walking away. He sighed, staring at the space she had vacated, then his jaw clenched in irritation as he slowly turned back to Crowley. “What the hell, man?” he snapped. “This is the third girl you’ve done this with. You’re supposed to be my wingman!”

“Well, to be fair, you pitched the idea by saying, and I quote, ‘I need your help. I need to get laid.’” Crowley fixed him with a meaningful look. “You give a guy all sorts of mixed signals.”

Dean blinked. “You didn’t _actually_ think-”

“Of course not,” he brushed it off. “Doesn’t change... never mind.” He sighed, turning back to his drink.

“Doesn’t change what?” he asked with a frown, his anger replaced by curiosity.

Crowley glared at the line of bottles in front of him. “Doesn’t change that I would have preferred that to be your meaning.”

Dean was silent while that sank in. Crowley sabotaging him was because he was... jealous? Oh. That actually made a lot of sense. He finished off his whiskey to buy himself some time to figure out what to say, then he turned back to Crowley. “What do you say we get out of here?” The words tumbled from his lips, not quite as smoothly as when he normally delivered that line.

Crowley blinked at him in surprise. “Are you sure?”

“Yeah.” And he was. He may have been suppressing what he felt for Crowley for longer than he even knew, but on some level he’d known about that for the past year, at least. “Sammy’s at the bunker, so... your place?”

He smiled as he held out his hand to Dean. “Come along, squirrel.”

Dean licked his lips nervously as he took the offered hand, unsure if the twisting in his stomach was from his nerves or being teleported. For his own peace of mind, he decided to go with being teleported. The fact that it didn’t fade after arriving at Crowley’s, well... he was soon too distracted to give it much thought.


	19. Your Soul

**Summary for the Chapter:**

> Prompt: Okay, so Crowley needed someone to make a deal with him so he could find Death and so in canon he makes a deal with Bobby, but AU where he makes that deal with Dean instead.

“The mission was a success, I take it?”

Dean spun around to find Crowley standing in the hotel room behind him. They had just gotten Pestilence’s ring, and he had been in the middle of packing up, while Sam and Castiel took care of some last-minute things at the hospital. 

“Yeah.” He subconsciously patted the pocket where the ring was tucked away. “Thanks for the info,” he added reluctantly.

“Oh, of course.” Crowley smiled as he stepped forward. “Of course, we’re not in the clear yet.”

“No,” Dean agreed. “Don’t suppose you know where Death’s at?”

He looked for a moment as though he was going to say he did, but then he shook his head. “No. Haven’t the foggiest.”

“Great. So, why’re you here?” he demanded.

“Because while I don’t _know,_ I can find out. There’s this little spell that I know.”

“And?” Dean pressed, immediately suspicious about the lack of information the demon was providing.

“Results are 100% guaranteed,” Crowley continued, and Dean’s suspicions continued to grow.

“So, what’s the catch?”

“Well, it’s a little bit embarrassing,” he explained as he walked closer. “There’s this... technicality.”

Dean arched an eyebrow, his stomach twisting slightly. “Yeah?”

“I need a little something to get the magic going.”

“Dammit, Crowley, get to the point,” he growled, though he had a sinking suspicion of where this was going.

“You make a wish. I can give you anything you want, darling - up to and including Death’s coordinates. All I need is your soul.”

Dean scoffed, shaking his head slightly as he looked away. Yeah, that was what he had thought. And Crowley was an idiot if he thought he was selling his soul for a second time.

“I’ve done more with less,” Crowley continued on with his sales pitch. “Let’s just say when they’re getting their Grammys, they shouldn’t all be thanking God. It’s worth it, Dean. Think.”

“I am thinking,” he snapped. “I’m thinking about the forty years I spent in Hell, and you’re insane if you think I’m going back there!”

“Of course you’re not,” he said soothingly as he took another step forward.

Dean’s eyes narrowed. “But-”

“I have no intention to keep your soul, Dean,” he explained. “I’ll give it right back.”

“And I’m just supposed to believe that?” he challenged. Demons lied - he knew that better than most. Then again... Crowley actually had come through for them so far.

“Yes.” Crowley took another step forward, placing him mere inches in front of him. Dean wondered vaguely how he had let him get so close without even realizing it. “Look, you’re right to be suspicious. But I’m your ally. Enemy of my enemy and all that. I need the devil back in his stock. In fact, my delicate ass depends on it. I promise you - temporary loan. I’ll give it. Right. Back.”

Dean sighed, struggling and failing not to look the demon in the eyes. “I can see why you’re King of the Crossroads,” he muttered. “You make quite the sales pitch.”

He chuckled. “I won’t let you go back to Hell, Dean - you have my word.”

The rational part of Dean’s brain was telling him not to make the deal - it was a recipe for disaster. But... there was just something about Crowley. He trusted him. And following that instinct had panned out before.... “Alright,” he sighed. “You’ve got a deal.”

Crowley smiled. “Excellent.” He reached out to cup the back of Dean’s head, pulling him forward. 

Dean had a panicked moment of wondering what the hell was going on before he realized and let his eyes slip shut as he leaned forward to press his lips against Crowley’s. He had expected to feel revulsion as their lips slip together - that was how it had been with the first crossroads demon he had made a deal with - but instead, it was... pleasant. Hell, he was actually enjoying it, even allowing Crowley to deepen the kiss.

Crowley hummed as he pulled away, licking his lips. “I’ll have that location for you straightaway. And if there’s anything _else_ I can do for you...” His eyes flickered over Dean’s body suggestively.

“How about we just worry about stopping the end of the world,” Dean suggested, though his cheeks were heating up slightly at Crowley’s implication.

Crowley smirked. “We can celebrate later, then. See you soon.” He teleported from the room before Dean could say that he wasn’t agreeing to ‘celebrating later.’ Well, surely he’d be able to get out of it when the time came... if he had the willpower, that was.


	20. Vampire

**Summary for the Chapter:**

> Prompt: AU where Dean never gets the vampire cure in season 6 and Crowley ends up taking him under his wing.

“Dammit, Sam!” Dean shouted as he rounded on his brother. “This is your fault!”

“I don’t know what you’re talking about, Dean!” Sam protested, holding up his hands in a placating gesture. “Just... just calm down, okay?”

“Why? Because I’m a vampire?” he all but growled as he took a step forward, his tongue darting out to lick the blood off his lips. “And who’s fault is that? Who let that fang turn me?”

“I didn’t! I...”

“Yes, you did.” Dean continued stalking forward, honestly not sure what would happen once he reached him. “And maybe you thought I’d last long enough to get the cure - but it doesn’t matter anymore, does it, Sammy?”

“No.” The desperation was gone from Sam’s voice. He was now completely calm as he reached behind him. “No, I suppose it doesn’t.”

He saw the flash of the machete as it swept through the air in an arc, and he lunged forward, his defensive instincts kicking in even though he knew it was too little too late. Even with everything that had happened, he hadn’t expected that Sam would actually try to kill him, and he had had his guard down. Even with his newly acquired agility, he didn’t think it would be enough.

So, when he didn’t feel his head being separated from his body, he looked up in surprise to find that the scenery had changed. His brother was gone, along with the girl he had.... Instead, he found himself in an old building, face-to-face with Crowley.

“Where the hell are we?” he demanded.

Crowley scoffed. “You’re welcome. If it weren’t for me, your darling brother would have chopped your head clean off.”

Dean shook his head slightly, looking away. “It’s what he should’ve done,” he muttered, even though it hurt to think of how willingly Sam had been about to kill him. He looked back to the demon. “Or can’t you see what I am?” He extended his fangs for emphasis.

He rolled his eyes. “Yes, you’re a vampire - woe is you. You’ve spared vampires before, have you not?”

He retracted his fangs, glaring at Crowley, though the person he was truly angry at was himself. “Yeah, because they weren’t hurting people! I just killed a girl back there!”

“Because you were starving yourself,” Crowley shot back, his tone exasperated. “If you eat - or drink - a balanced diet, you won’t have that problem.”

“Yeah, cause I have such a great history with balanced diets and moderation,” he spat.

“This is a little different,” he pointed out as he took a step forward. “Look, I know you have zero concern for your own well-being, but this diet is for the good of _others._ And that’s why I know you’ll stick to it.”

Dean had to admit he had a point. Still, his eyes narrowed suspiciously. “Why do you even care?”

Crowley shrugged. “Because if I don’t give you some guidance, you’ll go right back to Sam and let him kill you. And frankly, your death would be a tragic waste. So, let me help you.”

He said nothing. Accepting help from a demon was rarely a good move. Sure, it had panned out for him once - and sure the demon in that scenario had been Crowley - but the chances of it all ending well a second time were outstandingly slim. But... he knew he couldn’t do this on his own. And Sam seemed more willing to kill him than help him, so what other option did he have?

As Dean thought, Crowley wandered over to a fridge in the corner of the room and rummaged in it for a moment before pulling out a blood bag. “Thirsty?” he asked, waving it in Dean’s direction.

He licked his lips subconsciously. He hadn’t gotten very much blood from that girl - just enough to solidify his change before Sam had interrupted him. Before he could even think about it, he was walking forward, reaching for the blood.

Crowley smirked as he handed it over. “Don’t you worry, squirrel. I’ll take good care of you.”


	21. Discovered

**Summary for the Chapter:**

> Prompt: In which Sam is trying to find demon!Dean and he finds Dean and Crowley doing kareoke together in a pub and is absolutely appalled?

It was his first lead since Dean had disappeared, leaving nothing but a hastily scrawled note. _‘Sammy let me go.’_ Did he really think that he would be able to do that? After Sam had laid his dead body on his bed, then come back minutes later to find him gone? Of course he couldn’t _let him go._ He was his brother, and he was… alive? Well, it wouldn’t be the first time that Dean had come back from the dead, after all. It was possible. But why would he run out on him like this?

Sam had no idea what to expect when he walked into the bar that his search had led him to. Would he find Dean sitting at the bar, drinking a beer like everything was normal? Would he greet him casually, or yell at him for coming after him? Would he even be there at all, or was this just a false lead? And if he was there… what exactly had become of him? Even with all the terrible possibilities that had played out in his mind, though; nothing had prepared him for this.

He heard Dean before he saw him – his off-key singing that he would sometimes engage in whenever he was in a particularly good mood, or was at least trying to be. And then another voice joined his – a rough, British voice that Sam had never heard sing before, but he immediately knew who it belonged to.

He spun around to face the karaoke stage to see Dean and Crowley up there, singing ‘Close My Eyes Forever’ by Ozzy Osbourne and Lita Ford. The sight was so horrific that Sam couldn’t tear his eyes away. As Crowley sang the line, “And when we sleep would you shelter me in your warm and dark embrace,” Dean stepped behind him and pulled him against his front, the hand that wasn’t holding his mic trailing suggestively down his side.

“Yeah, they suck,” a waitress commented, clearly misreading the revulsion on Sam’s face.

“What?” he blinked at her, confused but grateful that she had managed to pull his attention away from his brother’s duet with the King of Hell.

“They’re regulars here,” she explained, nodding towards the stage. Sam reminded himself not to look. “Dean’s a stage hog – he’s the tall one, singing Ozzy’s part. This is the first time he’s managed to drag his boyfriend on stage with him, though.”

“His…” Sam cleared his throat. “His boyfriend?”

She shrugged. “Well, I’m assuming – they’re always together and do everything short of having sex in the middle of the bar. That being said, Dean does flirt around a lot, so if you wanted to try-”

 _“No!”_ he cut her off hastily. “No, no, god no. I just, uh… thank you.” He quickly turned on his heel and got out of the bar as quickly as possibly – but not before he caught sight of Crowley pulling Dean into a steamy kiss during an instrumental break.

When the door shut behind him, he leaned against the side of the bar and squeezed his eyes shut, that image emblazoned on the back of his eyelids. Dean had run off to be with _Crowley?_ That didn’t make any sense, and if someone had suggested that to him, he would had laughed at them. But he had just witnessed it with his own eyes. So, what the hell was he supposed to do now?


	22. Substitute for Whiskey

**Summary for the Chapter:**

> Prompt: Crowley pulling Dean into a heated kiss to distract him from pain. (Maybe Sam has to pop a bone back into a socket or something? That shit always looks like its painful af)

“What do you mean we’re out of whiskey?” Dean demanded. “How the hell are we out of whiskey?”

Sam made a bitch face that somehow still managed to retain a touch of sympathy. “Because you drank it all last night.”

Crowley gave an amused snort.

“This ain’t funny, Crowley!” Dean snapped, craning his neck to look at him from where he sat sideways in the motel room chair, gripping its back so hard that his knuckles were turning white. “Have you ever had a bullet dug out without anything to numb the pain?”

“Yes,” he retorted frankly. “As I recall, you stood there and watched.”

Sam sighed. “Dean, you’re just gonna have to grit your teeth and bear it. There’s nothing else for it.”

“Fine,” Dean grumbled, gritting his teeth as Sam knelt down to bring himself eye-level with his side, where he had been shot. 

He prepared himself for the pain of Sam digging into the wound, but suddenly a pair of lips collided with his own. He could still feel the pain of Sam fishing out the bullet, but at least he had something else to distract him from it. He returned the pressure of Crowley’s lips, focusing on the sensation. Eventually, the pain started to fade, and a few seconds later, Sam cleared his throat.

Crowley pulled away, a faint smirk on his lips. “I hope that was an adequate substitute for whiskey.”

Dean could feel his cheeks heating up slightly, and he was pointedly avoiding looking down at his brother, though he could imagine all too well the look he was giving them. “Nothing is an adequate substitute for whiskey. But… it wasn’t half bad,” he admitted.

Crowley’s smirk turned into a genuine smile. “Still hurt?”

“Well, yeah, I was shot,” he said with a small chuckle.

“Well, then…” He started to lean in again, but was distracted by the sound of Sam hitting the table as he shot to his feet.

“I’m out,” Sam muttered, turning on his heel and making a beeline for the door.


	23. Understanding

Crowley was not an easy person to be confined in the cab of a truck with for weeks on end, but Castiel had gotten used to it. He felt that he had a better understanding of the demon, and with that came knowledge of how to deal with his annoying tendencies. For example, if he showed annoyance, things were guaranteed to get worse – which might mean that his singing would grow louder, or his “small talk” would become even more vulgar – particularly when he was talking about Dean.

He wasn’t sure if the reason why sexual fantasies about Dean seemed to be Crowley’s favorite topic of conversation was because of the time they had spent together when Dean had been a demon, or if it was merely because that was what he figured would make Castiel the most uncomfortable. Even with how often it had come up, though; and with how well Castiel had gotten to know Crowley, he had never expected this.

He and Crowley hadn’t found any new leads on Lucifer, so they had decided to head to the bunker to see if they would have any more luck working with Sam and Dean. Castiel had just gotten back from a supply run with Sam, and when he had seen that Dean was no longer in the library, he had gone looking for him. Which was what had led to him standing in the doorway of Dean’s room, staring wide-eyed at Dean and Crowley tangled together on the bed.

He cleared his throat, and Dean yanked away from Crowley’s lips, his head snapping to face the door. “Cas… uh, hey man…” he spluttered as his cheeks turned slightly pink.

Crowley rolled his eyes as he placed a kiss on Dean’s neck before looking up at the angel. “You couldn’t knock?”

“I did not realize…” He suddenly became aware of the fact that it was probably inappropriate to stare, so he directed his gaze at the wall on the far side of the room, instead.

“I haven’t seen him in over a month. Did you really think I wouldn’t be jumping him the second we were alone?”

“You almost didn’t even wait till then,” Dean pointed out.

Castiel opened his mouth and closed it again as he realized that he had gotten it all wrong. All those things Crowley had been saying about Dean hadn’t been fantasies for the sake of annoying Castiel, they had been… their sex life.

“My apologies, I…” _I should go,_ was what he had been about to say, but then his eyes betrayed him and moved back to the bed. Dean was looking at Crowley now, and from the side of his face that Castiel could see, it looked like he was smiling fondly at him. But… when had this happened? And _how?_ And what _was_ it? “Is it just sex?” the words spilled from his mouth before he could stop them. “Or are you two… a couple?”

Dean turned back to Castiel, blinking at him in surprise. “I, um… we haven’t really…”

“We’re a couple,” Crowley interrupted his floundering.

Castiel didn’t miss the awed disbelief in Dean’s expression as he looked back at Crowley. It was clearly what he wanted; though, Castiel would never in a million years have thought that would be the case. He wanted to ask more questions, to try to figure out when everything he had thought he understood to be true had ceased to be so – because Dean hated all demons, and Crowley would never be in a serious relationship – but it looked as though they were quickly forgetting that he was still the room, and he knew he ought to get out of there before things escalated again. “I’ll… go then,” he muttered, taking a step backwards.

“Good,” Crowley said without taking his eyes off of Dean, at the same time that Dean muttered a distracted, “Okay.”

Castiel backed the rest of the way into the hall and closed the door. He stood there, frozen in shock for a good few seconds before he shook his head and managed to walk away. There was no way he’d be able to work out these answers on his own, so there was no point in trying. At any rate, he was sure to hear more about their relationship as soon as he and Crowley hit the road again. Not that that was necessarily a good thing.


	24. Glitter Bomb

**Summary for the Chapter:**

> Prompt: In which Dean and Crowley are drunk and decide to prank Sam,but the whole thing falls apart because they give the prank away by laughing too much.

Dean wasn’t entirely sure how it had started. He and Crowley had both had a few drinks, and they’d been talking about… past hunts? Or maybe it was just Sam in general. One way or another, Dean had brought up the time that Sam had been forced to fight a clown on his own, and when Dean had caught back up to him, he had been absolutely _covered_ in glitter.

“It was one of the greatest things I have ever seen,” Dean had sighed.

“You know, that’s an actual prank you can pull,” Crowley had said casually.

“What?”

“There’s a company that mails people cards that explode glitter over whoever opens it. And oddly enough, no demon was involved in its formation.”

Dean had let that sink in for a moment before a smile spread across his face. “You thinking what I’m thinking?”

However it had started, Dean and Crowley were now crouched, hiding in the corner of the library as Sam walked into the room and caught sight of the envelope with his name on it. They hadn’t had to wait for the company to mail the glitter bomb, of course; Crowley had just zapped himself into their headquarters, grabbed one, then zapped out.

Dean – who had had quite a few more drinks since he and Crowley had even begun to formulate this plan – couldn’t help but start laughing as Sam picked up the envelope curiously.

“Shhh,” Crowley shushed a bit too loudly for it to do much good. In other news, demons could, in fact, get drunk.

Sam’s gaze flickered up briefly, but then his attention moved back to the envelope, pulling out the card as he walked across the room. Dean and Crowley quickly shuffled to remain hidden, though the noise they made while doing so might have done more harm than good. Sam slowed as he reached their hiding place, then abruptly turned and opened the card over their heads, instantly covering them both in glitter.

“Oh, come on!” Dean shouted.

“Bloody hell, moose, do you know how much this suit costs?” Crowley complained, attempting to wipe the glitter off his jacket sleeves.

“Hey, you two brought this on yourselves,” Sam said with a shrug. “Maybe next time, don’t try pranking me while shit-faced.”


	25. New Year's Kiss

**Summary for the Chapter:**

> Prompt: Dean thinking the idea of a kissing at midnights on New Years is a stupid one, until Crowley does it then he thinks he could get used to that.

“Hey, handsome. You have someone to kiss at midnight?”

Dean turned and blinked at the woman in surprise. “Uh... no.” A quick glance around the bar showed that at five minutes till midnight, people were starting to couple off - and those who didn’t have someone appeared to be scoping out the prospects. He shook his head slightly. He would never understand why it was so damn important to start off the year kissing someone - it wasn’t like that was any indicator on how the rest of the year was going to go.

The lady smiled at him flirtatiously. “You wanna be my midnight kiss?”

“Um... look, I’m flattered, but... I’m gonna have to pass. Sorry.”

She did look disappointed, but she didn’t seem to take it too hard as she walked away, scanning the crowd for a new target.

It wasn’t that he hadn’t been attracted to her - she was hot - and maybe if he’d come to the bar seeking out a girl to go home with, it’d be different, but he just felt that it was stupid to kiss some random girl at midnight just so that they could both feel a little less lonely.

He sighed as he turned back to the bar and ordered another whiskey. Maybe he’d drink in the new year, instead.

So, thirty seconds till midnight, he watched the countdown on the screen with a drink in hand. He was so focused on the screen that he didn’t even notice the demon appear beside him as the clock reached the ten second mark. He couldn’t miss the hand grabbing hold of the front of his shirt as he shouted out “two” with the rest of the bar, though; leaving him with just one second to look at Crowley in surprise before he was dragged down into a kiss.

“Happy New Year!” those who didn’t have anyone to kiss shouted, but Dean hardly heard them, his entire world suddenly centered on Crowley’s lips.

When they finally broke apart, he was blinking rapidly, trying to figure out what the hell had just happened.

“Happy New Year, darling,” Crowley purred, snapping his fingers to vanish the whiskey that had spilled onto his suit.

Dean cleared his throat. “Yeah, uh... happy New Year.” His eyes darted back down to Crowley’s lips, hoping that he wouldn’t have to wait a year to do that again. Maybe New Year’s kisses weren’t so stupid, after all.


	26. Confession

**Summary for the Chapter:**

> Prompt: Dean drunk dialing Crowley and leaving a message about how much he loves Crowley (either before they got together or at the start of their relationship) and fiercely denying it the next day. ("I was drunk. You cannot hold me to anything I say!")

Dean ran a hand over his face as he forced himself to sit up, willing the pounding in his head to go away.

“Morning, squirrel,” a voice rang out from the corner of the room.

He groaned. The demon was the last thing he needed to deal with right now. “What the hell are you doing here, Crowley?”

“Thought I ought to come by,” Crowley said casually as he stood from the chair. With a snap of his fingers, Dean’s hangover vanished. “Respond properly.”

“Thanks,” he muttered, a bit reluctantly. “Respond properly to what?”

He raised an eyebrow. “You don’t remember calling me last night?”

A since of dread pooled in Dean’s stomach. “No. But I was drunk, so whatever I said-”

“You said,” Crowley interrupted him, his eyes dancing, “and I quote, ‘I kind of love you.’ You did say a few other things as well, but that was the gist of it.”

Silence filled the room as Dean’s brain launched into a chorus of, _Shit, shit, shit, shit, SHIT!_ “You don’t actually think...?” But the satisfied and mildly amused expression on Crowley’s face answered Dean’s question before he could finish it. “C’mon, man. I was drunk. You can’t hold me to anything I said!”

“You sounded pretty earnest.” He took a step forward, his expression becoming more serious. “The way I see it, maybe you do love me - maybe you don’t. But that profession came from somewhere, and I think it’s only fair that I give you my response.”

“Your response?” he asked slowly, his heart pounding furiously.

He inclined his head slightly. “I love you too, Dean. I have for over a year now.”

Dean couldn’t do anything but stare at him in shock, trying to wrap his brain around what he had just said.

“With that, I’ll leave you be,” Crowley continued, “let you figure out if drunk you may be a little more perceptive than your sober self.”

He opened his mouth to protest, but before he could said anything, Crowley was gone. Great. Just great. Now he was going to have to call him to confess his love _again._


	27. Defensive

**Summary for the Chapter:**

> Prompt: Dean getting kinda pissy about Dick insulting Crowley and claiming it's because "I'm the only one who gets to insult my boyfriend- I mean enemy. Definitely enemy."

“So, what went down between you and Dick, anyway?” Dean asked curiously. No way was Crowley helping them out of the goodness of his heart - something had to have gone down between him and the top dog Leviathan.

Crowley shrugged, feigning nonchalance whilst not quite looking at him. “I suggested we work together. He said something along the lines of he’d rather swim through garbage than shake hands with a bottom-feeding demon like me.”

 _“What?”_ Dean snapped, surprising even himself with the anger in his voice.

“And then he went on to describe just how much less than humans demons are - gold-digging whores, I believe he said.”

Sam snorted. “Can’t argue with him there.”

Crowley glared at the wall, while Dean rounded on his brother. “Hey!”

He blinked at him in surprise. “What?”

“We’re not going to agree with _Dick,”_ he protested hotly. “I mean, sure, that might fit most demons, but Crowley’s not most demons!”

Sam’s eyebrows shot up. “Dean... you call Crowley the lowest of the low at least once a week.”

“Yeah, well, I’m the only one who gets to insult my boyfriend!” His eyes grew wide as he realized what he had just said. “I mean enemy!” he amended hastily. “Definitely meant... enemy....” He trailed off, the utter shock that was still on Sam’s face communicating clearly just how unconvinced he was.

Crowley chuckled behind him. “Smooth, darling. I’m touched, though - never knew you could be so defensive over me.”

“Shut up,” Dean groaned, running a hand over his face. “I’m getting some air. _Neither of you_ follow me!” He stormed out the door of the cabin, slamming it shut behind him.

Before the door fully closed, he heard Crowley’s voice from inside the house, “So, moose - questions?”

This was just _great._


	28. Risk

**Summary for the Chapter:**

> Prompt: Dean waking up next to Crowley and thinking that he could very much get used to that

Falling asleep next to the King of Hell had definitely _not_ been Dean’s plan. That would have been a monumentally stupid idea - sleeping with a demon was one thing, physically _sleeping_ next to one, though... it was too much of a risk. 

Therefore, waking up next to Crowley, he should have felt disconcerted, he should have been immediately alert and on his feet. He certainly shouldn’t be feeling... peaceful. He shouldn’t find an easy smile spreading over his face as he was filled with the desire to never move again.

“Morning, squirrel,” Crowley said softly when he saw that he was awake.

“Morning,” he mumbled in reply as he tightened his arms around the demon, pulling himself closer to him.

“Sleep well?”

“Mmhmm.” It was the best night’s sleep he had had in some time, as a matter of fact. Hell, he couldn’t remember the last time he had slept through the night like that.

“Good.” He placed his hand under Dean’s chin, tilting his head up so that he could press their lips together.

If a lifetime of hunting had taught Dean anything, it was to trust his instincts. And right now, his instincts were telling him that he was completely safe. Furthermore, he was happy. So, maybe falling asleep next to Crowley was a risk, but he took risks all the time, and this was definitely one that he could get used to taking.


	29. Lucky

**Summary for the Chapter:**

> Prompt: Dean gets kidnapped by some monster and Crowley blows all of the monsters lackies away trying to find Dean and when he does Dean says he doesnt need Crowleys help but ends up (begrudgingly) thanking Crowley as he leaves.

Dean had been in tough binds before. This was nothing new, really - just another monster that had gotten the drop on him and taken him back to its top-secret lair to chain him up and taunt him before killing him. Only, they never seemed to get around to the killing part. If Dean were talking to someone else about it, he would say that it was because he was so much smarter than the sons of bitches that he hunted. But really, he knew he had just gotten lucky all those times. And one day that luck would run out. Who knew, maybe that day would be today.

There was a shout in the hall beyond the door, followed by a sickening crunch. Dean arched an eyebrow at the head of the werewolf pack standing before him. “You expecting company?” he asked without ceasing his attempt to subtly pick the lock of his handcuffs.

The werewolf spun around as the door banged open to reveal… Crowley? Dean couldn’t imagine what he would be doing here, but there was no mistaking the demon, staring down the werewolf with furious red eyes.

The werewolf crouched down, and Dean saw his fingernails lengthening into claws. That was as far as he got, though; because with a flick of his wrist, Crowley sent him flying into the wall with enough force to send him right through it. He stood regarding the hole in the wall for a handful of seconds before turning to Dean with a slight smirk, his eyes fading from red to their usual hazel. “Hello, darling.”

“Crowley,” he greeted him suspiciously. “What are you doing here?”

He arched an eyebrow at him. “Isn’t it obvious? I’m rescuing you.” His eyes flickered to the left. “Hold that thought.”

Dean opened his mouth to ask what he was talking about, but at that moment, the werewolf pulled himself through the hole in the wall, only to pull himself right into a silver blade as Crowley teleported in front of him, blade extended. “You took the wrong hunter,” his hissed.

Dean frowned, but didn’t comment as his handcuffs finally came free. “I had this handled, you know,” he said as Crowley turned back to him. “A few more seconds, and I would’ve had him.”

He rolled his eyes. “Sure you would’ve. And then you would have been ambushed by the group of werewolves that had been waiting just outside that door before I disposed of them.”

He glanced at the open door that Crowley was pointing at to see the hall strewn with corpses. He grimaced, not because of the sight, but because he didn’t want to admit that maybe he hadn’t had the situation under control, after all. Maybe he had needed Crowley to save him. 

He shook his head slightly. _Crowley_ had saved him. How the guy had even known that Dean had been captured, he had no idea, but somehow he had found out and had slaughtered a pack of werewolves to get to him. God knew Dean hadn’t asked him to do that. But relying on the demon was _not_ something he should get used to.

So, he turned to the door with every intention to leave without saying another word. But when he reached the doorway, he found himself stopping, glancing back at Crowley, who was watching him leave with a frown. He sighed reluctantly. “Thanks,” he muttered, then quickly left the room before Crowley had a chance to respond. 

He didn’t want to talk about what had just happened, he wanted to forget about it. Unfortunately, Dean knew himself pretty well. Just like he knew that he hadn’t been any smarter than these werewolves who were lying dead all around him - he had just gotten lucky, yet again - he knew that he wouldn’t be able to just forget what Crowley had done for him.


	30. Seal the Deal

**Summary for the Chapter:**

> Prompt: I've seen some posts in the Drowley tag how Crowley and Dean would bang the next time they made a deal. Since Crowley is the king of hell, and Lilith made people bang when she did deals. But I just can't see Crowley doing that. He's way classier than that. (Although this does not stop him from flirting with Dean if he ever asked about it. "So you still just kiss people to seal deals?""Yes... unless you wanted to go a little further." And Dean would stumble over his words with a red face)

When Dean realizes that he has to make a deal with Crowley, he remembers what Sam had told him about how when he’d nearly made the deal with Lilith, he would’ve had to sleep with her to seal it. It dawns on him that, with Crowley being the King of Hell, that’s probably the case for him, as well. It doesn’t lessen his resolve, though; and he doesn’t look too closely at why he’s not too bothered by the fact that he’s going to have to sleep with Crowley.

So, once he and Crowley have agreed on the terms of the deal, he starts unbuttoning his shirt.

Crowley raises his eyebrows. “Are you throwing in the strip tease for free, or was there something else you wanted from me?”

Dean frowns. “Don’t we... I mean, you’re a powerful demon... doesn’t that mean you seal your deals with sex?”

“Certainly not. I’m not that easy to get into bed.”

His cheeks are turning red. “I just thought... Lilith...”

“Well, I’m not Lilith, now am I?” He steps closer to Dean, smirking. “That being said, I think I might just have to make an exception for you.”


	31. Sleep Well

**Summary for the Chapter:**

> Dean probably passes out in random spots a lot while he's drinking so every time he does, Crowley picks him up and puts Dean into his own bed. (Or calls Sam at least, if he doesn't know where the brothers are staying)

I totally agree, but there has to be some occasion where, for one reason or another, he can’t get a hold of Sam, and he doesn’t know where the boys are staying. No one’s at the bunker to let him in, and he doesn’t want to just drop Dean off at some random hotel, so the way he sees it, there’s really only one option - take Dean to his place.

Dean wakes up in an unfamiliar room, laying on a bed with way to expensive sheets. After looking around in confusion for several seconds, he notices the tray of food on the bedside table, complete with pain pills for his hangover, and a note:

_Hope you slept well. I’ll be in shortly. Please wait for me, rather than running around my palace killing my demons. xo  
_

_\- Crowley_

He can’t help but smile a little bit as he takes the pills and starts in on his food.


	32. The Disappearing Brother

**Summary for the Chapter:**

> Prompt: Sam and Dean are working on a case and Sam is telling Dean about a lead he found when Crowley texts him a nude and then a text that say "I'm waiting ;)" And Dean is like YEAH I'LL CHECK IT OUT and rushes out of the room and Sam just sighs because he figures it's something Crowley related. (Especially 'cause this probably happens more than Dean would like to admit.)

The first time it happened, Dean got super flustered and stammered a reply that made no sense considering what Sam had asked him. Before Sam could ask what was going on, though, he had excused himself and darted from the room.

“Is it just me, or was that strange?” Castiel asked.

“Definitely strange,” Sam nodded.

The second time, Dean left a beer half drunk and a burger a quarter eaten, and Sam was worried that something might be wrong.

The third time, Sam started to figure it out. Dean had been less than motivated the past couple days, and Sam knew it had to do with how busy Crowley had been with Hell. So, when Dean had gone from dragging his feet on the case to rushing off to follow a lead on his own with all the energy of an overly-eager puppy, he had at least some idea of what was going on.

From there, he pieced together that every time Dean had suddenly disappeared over the past couple of months, it had been right after looking at his phone. Given that he had never seen Dean jump up so fast for a simple text - even from Crowley - he quickly decided that he didn’t want to know the details


	33. Guard Dogs

**Summary for the Chapter:**

> Prompt: Crowley's hellhounds protecting Dean because they recognize Dean as something that Crowley cares about.

There was a very distinct different between the snarl of a werewolf and that of a hellhound. Sure, most people wouldn’t be able to tell which was which, but Dean Winchester wasn’t most people, and _that_ hadn’t come from the werewolf he was hunting. So, since he clearly didn’t have enough problems, he was now up against a werewolf _and_ a hellhound. 

Actually, make that two hellhounds.

Dammit.

His silver bullets wouldn’t do squat against hellhounds. He needed to get back to the car - preferably _before_ getting torn to shreds. Again. He shuddered at the memory.

He was halfway back to the car when he was jumped. It was his own fault, really. The hellhounds had made him paranoid, and he had become more focused on surviving them than the creature he had been hunting in the first place.

His gun went flying out of his hand as his back hit the ground, and he couldn’t help but think that after all he had survived, death by werewolf certainly wasn’t how he had thought he would go. Before the werewolf could land the killing blow, though, its head was torn from its body... seemingly by nothing.

It took Dean a moment to process what had just happened as he stared at the werewolf’s corpse, watching as bits of it disappeared into the air as the hellhounds devoured it. He was just weighing his chances of being able to slip away unnoticed when a familiar voice spoke from behind him.

“Good girls.”

Hellhounds all but forgotten, Dean’s head snapped around to the demon behind him. “Crowley? What the hell are you doing here?”

“Keeping you alive. You’re welcome, by the way.” He reached a hand out to pat one of the invisible hounds on the head.

“You sent the hellhounds... to protect me?” he asked incredulously.

“Of course. I can’t be with you all the time. It gives me peace of mind.” He shrugged nonchalantly as if he hadn’t just admitted that he was worried about Dean whenever he wasn’t by his side.

Dean found himself smiling slightly at that, even though the entire situation did weird him out slightly. “That’s... kind of sweet.”

“Yes, well, don’t spread it around.” He offered out a hand to help him up. “We should get moving. Juliet just caught a scent - there’s another werewolf out there.”


	34. Enemy of My Enemy

**Summary for the Chapter:**

> Prompt: "Don't fight me now cause you might need me later."

There had to be a better option. Sure, there was the enemy of my enemy is my friend, and all that crap, but Dean was pretty sure that statement didn’t apply when said ‘enemy of my enemy’ was a demon. And yet, here they were, teaming up with Crowley against a group of demons the King of Hell _claimed_ had gone rogue. What could go wrong?

Crowley had offered to run down a new lead while Sam and Dean continued on the lead they had been working on, but Dean wasn’t about to let Crowley out of his sight. So, Sam went off to talk to the wife of the latest victim, while he went with Crowley went to investigate an old haunt of the demon he was pretty sure was in charge of this rebellion.

“One would think,” Crowley mused as they walked together, “that after all this time, you might start to trust me a little bit.”

“Not a chance,” Dean spat. “You’re a demon, Crowley. I’d rather kill you than work with you.”

He raised his eyebrows. “Rude. You can’t really mean that.”

“Oh, but I do.” He raised his hand that was currently holding the demon knife and looked at Crowley pointedly. “You want me to prove it?”

He just rolled his eyes. “Don’t fight me now, cause you might need me later, darling.”

“I never need you,” he grumbled, but he lowered his arm all the same.

It was about half an hour later that they were ambushed. About a half dozen demons came at them, and Dean found himself not as surprised as he would have thought when he saw that Crowley was, in fact, fighting on his side.

Dean was pretty sure there were only one or two demons left when he was shoved against the wall by his throat, his knife slipping from his fingers. He struggled for oxygen for a good thirty seconds, and then the demon flickered and dropped to the ground, releasing him. Behind him stood Crowley, the demon knife in his hand.

“Told you you’d need me later,” he said as he offered the knife out to him.

“Thanks,” he muttered reluctantly, his eyes scanning the room. The floor was littered with demon corpses, but then he noticed that one was breathing, his hands tied behind his back. “That the leader?” he asked, nodding towards him.

“I believe so,” Crowley said with a cruel smile as he turned to look at him. “You want first go at him, or shall I?”

Dean chuckled. “You’re the one he betrayed,” he pointed out with a half-shrug.

“So, you _do_ care,” he mocked as the sauntered over and lifted the other demon up by the collar of his shirt.

Dean shook his head slightly in exasperation as he leaned back against the wall, watching Crowley start in on him. Maybe they didn’t need a better option, after all.


End file.
